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Holiday houses in Cerchiaia

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Top-rated holiday rentals in Cerchiaia

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 281 reviews

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

Top Guest favourite
Home in Siena
4.97 out of 5 average rating, 195 reviews

Podere Piazza house with panoramic view

Podere Piazza is an estate, has its origin in the 15th century. The vacation home was built at the beginning of the 17th century. Podere Piazza was the residence of Alessandro Cervini degli Spannocchi, who was appointed Archbishop of Siena on May 29, 1747. He was a Nobile di Montepulciano and Patrizier of Siena. The buildings of Podere Piazza still bear his coat of arms today. This also explains our little church, at the road junction, in front of it to the right to the pine avenue and to the left into the driveway.

Superhost
Apartment in Siena
4.87 out of 5 average rating, 15 reviews

The little house

We open the doors of our house in the Siena countryside, 7 minutes by bus from the centre (stop 2 minutes away). A small, functional nest, designed to make you feel at home, ideal for couples or singles. It offers a double bedroom and a small bedroom with a sofa bed: to ensure total comfort, we recommend it for 2/3 guests, but it can accommodate up to 4. The kitchen is spacious and equipped; the bathroom, although small, is complete with everything. Free parking in front of the house, no limited traffic zone.

Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 516 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 154 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 18 reviews

La Mattonaia, home with free private parking

Just outside the city walls, this bright apartment with a garden is served by city buses to the historic center, stopping right outside the gate. Strada Massetana Romana is home to a wide range of shops: supermarkets, a pharmacy, bars, a bank, clothing stores, and more. The apartment comprises a spacious double bedroom, a bathroom with shower, a fully equipped kitchen, and a spacious living room. Guests have access to convenient free parking within the fenced property with an automatic gate.

Guest favourite
A cozy bedroom features a spacious bed with a textured blue blanket, complemented by multiple pillows. Natural light enters through two windows with sheer curtains, illuminating the room's wooden beams and terracotta tile flooring. A wardrobe holds clothing, while a potted plant adds a touch of greenery.
Apartment in Siena
4.95 out of 5 average rating, 111 reviews

Apartment in historic Villa in Siena_"Il Campo"

The apartment "Il Campo" is part of "Villa il Borghetto - Apartments". Villa il Borghetto offers apartments in Siena in a historic Villa, with the guarantee of an authentic hospitality, thanks to the family management of the "landlords". Villa il Borghetto has been designed to accommodate families wishing to experience Siena as a local, offering a convenient location to visit Siena without giving up the view of the Typical Tuscany rolling hills and the convenience of a free private parking.

Top Guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena
4.98 out of 5 average rating, 112 reviews

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 18 reviews

Luxury penthouse with a view of Piazza del Campo

There are many houses in Siena. But very few can say they are here. Overlooking the city's most iconic square, this penthouse offers a rare experience: waking up with the golden light that caresses the Palazzo Pubblico and falling asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you are immersed in history, among restaurants, wines and timeless atmospheres.

Superhost
The exterior area showcases a spacious garden with well-maintained greenery. A stone pathway leads to a two-story building, which features multiple windows. A dining set with four chairs occupies a patio space, accompanied by a tree and decorative elements, creating a serene outdoor setting.
Apartment in Siena
4.94 out of 5 average rating, 193 reviews

Studio with Garden (2 km from the city center)

La Coroncina is situated just 2 km from the historical center, 2.7 km from Piazza del Campo, 2.9 km from Piazza del Duomo and 2.6 km from National Picture Gallery Siena. The structure is in a peaceful but very central location in the south of Siena with bus stops at few meters. Within little driving distance you may find a large grocery stores, restaurants and bars. Breakfast is optional and costs 15 euro per person

Guest favourite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Apartment in Monteroni d'Arbia
4.94 out of 5 average rating, 283 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Guest favourite
A cozy bedroom features a spacious bed with a patterned duvet cover. Large windows provide natural light, and elegant curtains frame the view. A subtle accent wall adds character to the room, complemented by tasteful artwork and an air conditioning unit for comfort.
Apartment in Siena
4.95 out of 5 average rating, 43 reviews

Strategic Apartment

A new renovated apartment, Perfect for who wants to visit siena and the countryside as well ( Chianti, Montalcino ecc). The historic city center reachable by car in 5 minutes. You can park your car at the gas station near the apartment. *** IF YOU DON’T HAVE A CAR, IT WOULD BE VERY INCONVENIENT.

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